Title: Book the Best ADVENTURE Hotels in Near South Side in 2026 | Expedia.ca

[Near South Side Travel Guide](https://expedia.ca/Chicago-Near-South-Side.dx6132399)[Vacation Rentals in Chicago](https://expedia.ca/Chicago-Vacation-Rentals.d178248.Travel-Guide-VacationRentals)[Flights to Chicago](https://expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Near South Side Car Rentals](https://expedia.ca/Car-Rentals-In-Near-South-Side.d6132399.Car-Rental-Guide)[Near South Side Vacations](https://expedia.ca/Near-South-Side.d6132399.Destination-Travel-Guides)

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![](https://images.trvl-media.com/place/6132399/d6571aed-ec1a-4cde-82c6-09026eacaa3d.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check availability on Near South Side Hotels & Resorts for Couples

Tonight

[Feb 4 - Feb 5](https://www.expedia.ca/Hotel-Search?regionId=6132399&startDate=2026-02-04&endDate=2026-02-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Feb 5 - Feb 6](https://www.expedia.ca/Hotel-Search?regionId=6132399&startDate=2026-02-05&endDate=2026-02-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6132399&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6132399&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Near South Side adventure hotels

![Exterior](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/f1a5921f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/c35b1006.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/6b27f192.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Food and drink](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/e9e7f382.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### voco Chicago Downtown - Riverwalk by IHG

[](https://www.expedia.ca/Chicago-Hotels-Voco-Chicago-Downtown.h76459163.Hotel-Information)

Downtown Chicago

8.8/10

Excellent

(3,654 reviews)

"Great place to stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

suleman

CA $171

CA $200 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Chicago-Hotels-Voco-Chicago-Downtown.h76459163.Hotel-Information)

![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/109a2156.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/6ec865cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/77822130.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Wade

[](https://www.expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information)

Downtown Chicago

8.4/10

Very good

(1,651 reviews)

"Lovely room, beautiful hotel, wonderful staff, ideal location to navy pier & Michigan Ave. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Norah

CA $149

CA $175 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d891f039.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/b58d9761.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![City view from property](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/2b1c0fd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d46a8a4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Felix River North/Magnificent Mile

[](https://www.expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information)

Downtown Chicago

8.2/10

Very good

(2,549 reviews)

"I liked the hotel. The staff was very courteous and friendly. The room was cute. The location is fantastic."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Equilla

CA $82

CA $138 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information)

![55-inch LCD TV with cable channels, TV, pay movies](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/bb12c333.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/0e6690c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/325d0c28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/bf403e2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### L7 Chicago by LOTTE

[](https://www.expedia.ca/Chicago-Hotels-L7-Chicago-By-LOTTE.h4200.Hotel-Information)

Downtown Chicago

9.6/10

Exceptional

(3,620 reviews)

"Rooms were nice and clean and staff was super friendly."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

David

CA $203

CA $239 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Chicago-Hotels-L7-Chicago-By-LOTTE.h4200.Hotel-Information)

![Bar (on property)](https://images.trvl-media.com/lodging/6000000/5210000/5204900/5204897/9c44ca76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/6000000/5210000/5204900/5204897/9833019f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/6000000/5210000/5204900/5204897/3f6518d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/6000000/5210000/5204900/5204897/612465b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ivy Boutique Hotel

[](https://www.expedia.ca/Chicago-Hotels-Ivy-Boutique-Hotel.h5204897.Hotel-Information)

Downtown Chicago

8.6/10

Excellent

(1,087 reviews)

"I always stay here when in town. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jeffrey

CA $98

CA $115 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Chicago-Hotels-Ivy-Boutique-Hotel.h5204897.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/2806d344.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/12cef3af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/c6f61b94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Room, 2 Queen Beds, Accessible, City View (Mobility, Accessible Tub)](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/8acc816e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Chicago Dwtn - The Mart by IHG

[](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Dwtn-Wolf-Point.h5467.Hotel-Information)

Downtown Chicago

8.8/10

Excellent

(2,155 reviews)

"Great location"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Adam

CA $150

CA $176 total

includes taxes & fees

Feb 6 - Feb 7

[](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Dwtn-Wolf-Point.h5467.Hotel-Information)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/w3837h2557x3y3-ef0f356b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/3932c1a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/95b10764.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/8b216cef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Thompson Chicago, by Hyatt

[](https://www.expedia.ca/Chicago-Hotels-Thompson-Chicago.h26076.Hotel-Information)

Downtown Chicago

9.2/10

Wonderful

(1,309 reviews)

"Love this hotel, right in the middle of a great area re: restaurants, bars, night scene, etc. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Yoshio

CA $184

CA $256 total

includes taxes & fees

Mar 4 - Mar 5

[](https://www.expedia.ca/Chicago-Hotels-Thompson-Chicago.h26076.Hotel-Information)

![Premium bedding, pillowtop beds, minibar, in-room safe](https://images.trvl-media.com/lodging/1000000/1000000/992500/992500/6044b661.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/1000000/992500/992500/af017848.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/1000000/992500/992500/1089534d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/1000000/992500/992500/a8fb5620.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kinzie Hotel

[](https://www.expedia.ca/Chicago-Hotels-Kinzie-Hotel.h992500.Hotel-Information)

Downtown Chicago

9.2/10

Wonderful

(2,078 reviews)

"Clean room, wonderful staff, great location, good continental breakfast. Fabulous stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cassandra

CA $158

CA $239 total

includes taxes & fees

Feb 5 - Feb 6

[](https://www.expedia.ca/Chicago-Hotels-Kinzie-Hotel.h992500.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/30000/23500/23481/6c5eafdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/30000/23500/23481/ad5db3a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![55-inch plasma TV with cable channels, TV, DVD player](https://images.trvl-media.com/lodging/1000000/30000/23500/23481/5e134874.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/23500/23481/b45c5a5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

[](https://www.expedia.ca/Chicago-Hotels-THE-MIDLAND-HOTEL.h23481.Hotel-Information)

Downtown Chicago

8.2/10

Very good

(1,001 reviews)

"Super clean rooms , nice down stairs , loved the bathroom "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kaiya

CA $150

CA $177 total

includes taxes & fees

Feb 21 - Feb 22

[](https://www.expedia.ca/Chicago-Hotels-THE-MIDLAND-HOTEL.h23481.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/30000/26000/25929/4e2c019f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Suite, Multiple Beds, Lake View (King and Queen Bed)](https://images.trvl-media.com/lodging/1000000/30000/26000/25929/1d8943f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/26000/25929/w3839h3333x0y0-56c69498.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/26000/25929/db8ea890.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

[](https://www.expedia.ca/Chicago-Hotels-Sonesta-ES-Suites-Chicago-Downtown.h25929.Hotel-Information)

Downtown Chicago

8.6/10

Excellent

(2,374 reviews)

"Can't wait to go back love the hotel and the location was great."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

eyulonda

CA $124

CA $146 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/Chicago-Hotels-Sonesta-ES-Suites-Chicago-Downtown.h25929.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-18&endDate=2026-02-19&regionId=6132399&adults=2&nearby_group=recreation&sort=RECOMMENDED&openPlayBack=true)

## Top Near South Side Hotel Reviews

![The Royal Sonesta Chicago Downtown](https://images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg)

### The Royal Sonesta Chicago Downtown

10/10 Excellent

"Very nice experience at Royal Sonesta. Friendly staff. Comfortable , clean accommodations. Nice view of Chicago. "

[](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information)

![Hotel Felix River North/Magnificent Mile](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d46a8a4d_y.jpg)

### Hotel Felix River North/Magnificent Mile

10/10 Excellent

"My sister and her friends had a great time staying on NYE. Convenient location to festivities, friendly staff, and a 24 hrs Walgreens. "

[](https://expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information)

![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg)

### Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent

"Rooms was clean, staff was amazing, and loved the breakfast! Best breakfast I’ve had at a hotel. "

[](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information)

![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg)

### Hilton Chicago

10/10 Excellent

"Some of the nicest people you'll ever meet! Excellent location for a Bears game stay, walking distance to Soldier Field."

[](https://expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information)

![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg)

### Congress Plaza Hotel

10/10 Excellent

"Great a+++"

[](https://expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information)

![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg)

### Pendry Chicago

10/10 Excellent

"Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium."

[](https://expedia.ca/Chicago-Hotels-Pendry-Chicago.h982552.Hotel-Information)

![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/74c2f40d_y.jpg)

### LondonHouse Chicago, Curio Collection by Hilton

10/10 Excellent

"Staff was friendly and loved the decor at this hotel…will definitely be staying again"

[](https://expedia.ca/Chicago-Hotels-LondonHouse-Chicago.h12786616.Hotel-Information)

![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg)

### Hilton Chicago/Magnificent Mile Suites

10/10 Excellent

"Every thing was excellent and the staff too"

[](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information)

![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982_y.jpg)

### Eurostars Magnificent Mile

10/10 Excellent

"clean nice room, comfy bed, really nice rainfall and handheld showers, nice bathroom products. good location"

[](https://expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information)

## Frequently asked questions

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- [Hotels near Field Museum of Natural History ](https://www.expedia.ca/Field-Museum-Of-Natural-History-Hotels.0-l6065115-0.Travel-Guide-Filter-Hotels)
- [Hotels & Resorts for Couples in Magnificent Mile ](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels-Couples-Resorts-Hotels.0-n800025-0-tCouplesResortsHotels.Travel-Guide-Filter-Hotels)
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- [Hotels near Northerly Island Natural Area ](https://www.expedia.ca/Northerly-Island-Natural-Area-Hotels.0-l6125418-0.Travel-Guide-Filter-Hotels)
- [Cheap Hotels in Prairie District ](https://www.expedia.ca/Prairie-District-Chicago-Hotels-Cheap-Hotels.0-n553248635976473159-0-tCheapHotels.Travel-Guide-Filter-Hotels)
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- [Hotels near Soldier Field ](https://www.expedia.ca/Soldier-Field-Hotels.0-l6058043-0.Travel-Guide-Filter-Hotels)
- [Beach Hotel Hotels in South Loop ](https://www.expedia.ca/South-Loop-Chicago-Hotels-Beach-Hotel.0-n6130108-0-tBeachHotel.Travel-Guide-Filter-Hotels)
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- [The Loop Hotels ](https://www.expedia.ca/The-Loop-Chicago-Hotels.0-n800024-0.Travel-Guide-Filter-Hotels)
- [Hotels near Wintrust Arena ](https://www.expedia.ca/Wintrust-Arena-Hotels.0-l553248634328853320-0.Travel-Guide-Filter-Hotels)

- [Flights to Chicago ](https://www.expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)
- [Flights from Toronto (YYZ) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago)

- [Visit Downtown Chicago ](https://www.expedia.ca/Chicago-Downtown-Chicago.dx6350699)
- [Visit Prairie District ](https://www.expedia.ca/Chicago-Prairie-District.dx553248635976473159)
- [Visit South Loop ](https://www.expedia.ca/Chicago-South-Loop.dx6130108)
- [Visit The Loop ](https://www.expedia.ca/Chicago-The-Loop.dx800024)
- [Chicago Vacations ](https://www.expedia.ca/Chicago.d178248.Destination-Travel-Guides)
- [South Loop Vacations ](https://www.expedia.ca/South-Loop.d6130108.Destination-Travel-Guides)

- [Advantage Rent-A-Car Rental Cars in South Loop ](https://www.expedia.ca/Advantage-Rent-A-Car-Car-Rentals-In-South-Loop.d6130108-c3.Car-Rental-Guide-Suppliers)
- [Budget Rental Cars in Central Station ](https://www.expedia.ca/Budget-Car-Rentals-In-Central-Station.d6132250-c39.Car-Rental-Guide-Suppliers)
- [Enterprise Rental Cars in South Loop ](https://www.expedia.ca/Enterprise-Car-Rentals-In-South-Loop.d6130108-c15.Car-Rental-Guide-Suppliers)
- [Sixt Rental Cars in South Loop ](https://www.expedia.ca/Sixt-Car-Rentals-In-South-Loop.d6130108-c35.Car-Rental-Guide-Suppliers)

- [Things to do in Chicago ](https://www.expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)

- [Book Hotels in Near South Side on Expedia.com ](https://www.expedia.com/Near-South-Side-Chicago-Hotels-Couples-Resorts-Hotels.0-n6132399-0-tCouplesResortsHotels.Travel-Guide-Filter-Hotels)